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基于迈克尔加成反应和分子内电荷转移机理设计合成了一个比率型荧光探针MSP,并将其用于对亚硫酸盐和硫化氢的区分检测。强吸电子基团丙二腈的引入,使得探针的吸收和发射波长红移,同时极大地提高了探针与亚硫酸盐的反应速率,实现了对亚硫酸盐的快速检测。当反应时间延长至3 h时,硫化氢的存在使得探针的荧光波长蓝移至510 nm且强度显著增强,探针在两个波长下的荧光比率(I510/I690)增强约260倍,实现了在不同响应时间和不同光谱通道区分检测亚硫酸盐与硫化氢的目的。该探针具有良好的选择性和竞争性,可分别利用吸收强度比值(A464/A572)和荧光强度比值(I510/I690)定量检测亚硫酸盐和硫化氢,两者检出限分别为0.95μmol/L和0.6μmol/L。该探针还能用于对活细胞内亚硫酸盐和硫化氢的荧光成像。 相似文献
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以4-三氟甲基-7-羟基香豆素为荧光母体,4-溴丁酰基为识别基团,合成了一种基于分子内电荷转移机制的肼荧光探针XS-1,其结构经核磁共振氢谱(1H NMR),核磁共振碳谱(13C NMR)和高分辨质谱(HRMS)确证,通过荧光发射光谱研究了探针对肼的响应性能。结果表明,在磷酸盐缓冲液(10 mmol,pH7.4)中,探针XS-1能通过荧光增强作用识别肼,并具有很好的选择性和抗干扰能力,检出限为0.11μmol/L。探针XS-1具有斯托克斯位移大(144 nm)、线性范围宽(0~400μmol/L)、合成简便以及能在水相中检测肼等优点,并已成功用于实际水样中肼的定量检测。 相似文献
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硫化氢(H2S)是继一氧化碳和一氧化氮之后,第三种可在生命体内发挥生理作用的内源性气体信号分子。该气体分子在心血管和神经系统中担负着重要的生理病理调节作用。因此,选择性识别和高灵敏检测生物体内的H2S具有十分重要的生物医学意义。在生物检测技术手段中,荧光探针法具有选择性好、灵敏度高、对生物样品损伤小以及可实现实时原位检测等独特的优势,故应用荧光探针法检测细胞内H2S浓度的变化是近年来研究热点之一。本文依据荧光探针与H2S之间的化学反应类型,将近三年来所研发的H2S荧光探针按照其母体荧光团进行分类和总结,综述了H2S荧光探针的研究进展,概述了相关荧光探针的设计理念、检测机理及生物应用,探讨了探针的结构和性能之间的关系,最后展望了H2S荧光探针的发展趋势和应用前景。 相似文献
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以叠氮基为识别基团,4.4'-联苯二甲酸为初始原料,合成了一种可用于H_2S检测的联苯类比率型荧光探针2-叠氮基-4,4'-联苯二甲酸乙酯(WN),并通过~1H NMR、~(13)C NMR以及MS等技术手段对其结构进行了表征。以检测水溶液中硫化氢为目的,系统地研究了其荧光特性。研究结果表明,WN对硫化氢具有高选择性和灵敏度,且对生物硫醇(Cys,Gsh)、活性氧化物(H_2O_2,ClO~-)、各种阴阳离子(H_2PO_4~-,SO_4~(2-),Cl~-,HCO_3~-,CO_3~(2-),Mg~(2+),Zn~(2+),K~+,Ca~(2+),Na~+)有很强的抗干扰能力,在较宽的pH值范围内,仍然表现出良好的荧光性能,在1.1~350μmol/L范围内,NaHS的浓度与荧光强度呈现良好的线性关系,相关系数R~2=0.9943,检出限度为1.07×10~(-6)mol/L。通过对3种不同水样的测试,表明探针WN在水体中H_2S的检测方面具有一定的应用意义。 相似文献
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Tong Hong Song Cheng Xuefang Zhong Yiwei Zuo Yiming Dong Zhichuan Shi Zhigang Zhao 《中国化学会会志》2023,70(2):136-144
A novel dicoumarin-derived hydrogen sulfide (H2S) selective fluorescent “turn-on” probe 3-(2,4-dinitrobenzenesulfonate)-dicoumarin (DC-HS) created by covalent bonding between the 2,4-dinitrobenzenesulfonyl (DNBS) and the 3-hydroxy-dicoumarin (DC-OH) units. Upon the addition of H2S, the probe DC-HS solution's fluorescence significantly increased, and its appearance is changed from practically colorless to brilliant yellow. Probe DC-HS also showed significant fluorescence amplification that was quantitatively detectable in the concentration range of 0–1.5 μM and had a low detection limit or limit of detection of 0.2 nM. Moreover, with a high recovery rate and excellent accuracy, the developed fluorescent molecule was used successfully for the analysis of H2S in red wine samples. 相似文献
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《Journal of Coordination Chemistry》2012,65(21):3487-3499
AbstractA fluorescent probe 1 containing copper(II) had been designed and synthesized based on a coumarin derivative. The molecular structure of probe 1 was characterized by 1H NMR, HRMS, IR, and elemental analysis. The interactions of 1 with biologically important anions and amino acid were determined by UV–Vis, fluorescence, and HRMS titration experiments. Results indicated that probe 1 showed the highest binding ability for HS? among studied anions (AcO?, H2PO4?, F?, Cl?, Br?, and I?) and cysteine in pure dimethyl sulfoxide (DMSO) and HEPES buffer solution. As we expected, the response of UV–Vis spectra in aqueous solution was stronger than that of pure DMSO solvent. In addition, the binding ability for HS? was not hindered by the existence of other anions. HRMS titration experiment showed that the interacted mechanism was that the copper(II) ion in 1 was captured by HS? and then free ligand released. Furthermore, the detection limit of probe 1 with HS? was carried out through UV–Vis titration showing 1 to be highly sensitive for HS?. 相似文献
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This paper presents a series of first-and second-generation click-modified coumarin-based fluorescent probes for thiols.These molecules demonstrate high turn-on fluorescent response and good selectivity towards aromatic thiols over other relevant reactive sulfur species,reactive oxygen species and common nucleophiles.Moreover,probe 1a can detect thiols in the reduced rabbit plasma sample.Therefore,this approach provides a particularly impressive tool for detecting thiol in biological systems. 相似文献
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硼酸及硼酸酯类过氧化氢荧光探针的最新研究进展 总被引:2,自引:0,他引:2
生物新陈代谢过程中产生的过氧化氢(H2O2)是生命活动所必需的,但是过量过氧化氢的存在可以引发多种疾病,因此对体内过氧化氢的检测具有重要意义.采用荧光探针法,借助激光共聚焦成像技术能够实现对活细胞和组织内的过氧化氢"实时、可见、定量"的检测,为深入阐明过氧化氢在生理和病理过程中所起的作用提供了一个重要手段.本文按荧光探针的结构分类,对近几年来以硼酸及硼酸酯基团作为荧光开关的具有高选择性和灵敏度的过氧化氢荧光探针进行了综述,主要探讨其设计思想、作用机制及应用,为过氧化氢探针的设计提供了新思路. 相似文献
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Based on the mechanism of H2O2-mediated hydrolysis of sulfonates, two fluorescein disulfonates compounds (FS-1 and FS-2) were designed and synthesized as
the highly selective and sensitive fluorescent probes for imaging H2O2 in living cells. The probes were detected with elemental analysis, IR, 1H NMR and 13C NMR. Upon reaction with H2O2, the probes exhibit strong fluorescence responses and high selectivity for H2O2 over other reactive oxygen species and some biological compounds. Furthermore, the sulfonate-based probes, as novel fluorescent
reagents, are cell-permeable and can detect micromolar changes in H2O2 concentrations in living cells by using confocal microscopy.
Supported by the National Basic Research Program of China (Grant No. 2007CB936000), the National Natural Science Funds for
Distinguished Young Scholar (Grant No. 20725518), Major Program of the National Natural Science Foundation of China (Grant
No. 90713019), the National Natural Science Foundation of China (Grant No. 20875057), the Natural Science Foundation of Shandong
Province, China (Grant No. Y2007B02), and the Science and Technology Development Programs of Shandong Province, China (Grant
No. 2008GG30003012) 相似文献
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基于磺酸酯的荧光探针用于活细胞内过氧化氢的成像检测 总被引:1,自引:0,他引:1
基于过氧化氢(H2O2)特异性催化水解磺酸酯,设计合成了新型绿色荧光探针:荧光素二磺酸酯(FS—1)和二氯荧光素二磺酸酯(FS-2)两种螺环内酯型化合物,用于活细胞内过氧化氢的检测.探针结构由元素分析、IR、^1H NMR及^13C NMR表征.实验表明:探针FS-1和FS-2在模拟生物体系中检测过氧化氢具有良好的选择性和灵敏度,且线性范围较宽.细胞成像显示:探针FS-1和FS-2用于PMA刺激或外加不同浓度H2O2孵育的小鼠腹膜巨噬细胞均呈现明亮的绿色荧光,且能对细胞内H2O2微摩尔级浓度变化产生响应,证明两探针均具有良好的膜渗透性、高的选择性及良好的灵敏度.该方法的建立对研究生物体内H2O2的产生,H2O2导致的各种疾病机制及H2O2介导的信号转导途径具有重要的理论及实际意义. 相似文献
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Hye Gun Ryu Subhankar Singha Yong Woong Jun Ye Jin Reo Kyo Han Ahn 《Tetrahedron letters》2018,59(1):49-53
Hydrogen sulfide (H2S) is an endogenous gasotransmitter and plays intriguing biological roles. To study the biological role of H2S, efficient fluorescent probes are in great demand. For imaging of H2S in deep-tissue, a two-photon probe that emits in the red wavelength region is of choice to avoid the autofluorescence from intrinsic biomolecules. Here, we disclose such a probe, which, developed based on an acetyl benzocoumarin fluorophore, can be excited at 900?nm under two-photon excitation and emit in the red region. The probe shows high reactivity, selectivity, and sensitivity in in vitro assays. Two-photon microscopic imaging of H2S in HeLa cells aided by the probe demonstrates that it is potentially useful to study H2S level changes in cells and tissues influenced by external stimuli. 相似文献